I agree with what nearly everyone else stated. A logo or a hot item doesn't make you fashionable, but selectively purchasing quality items definitely helps. I rarely have access to current-season designer wear, but by taking the time to skim through the collections, I can keep a mental catalogue of looks that I hope to acheive. For example, with the upcoming fall, I saw a lot of greys and oxbloods. Those colors will be on the top of my shopping list. I may not be able to get any of the actual pieces until they show up on YOOX in a year or two, but I can have the general look.
The classic example of money not equaling style occured when I was in Milan last Summer. I knew I wasn't going to buy much there (because I was planning an outlet trip the next weekend), but I was dying to see all of the boutiques. There was an inordinate amount of older, monied men who had no clue what they were purchasing. I was in Moschino or Missoni and a mid-60s, overweight American man was slumped in a chair while his wife held clothes up in front of him. "This would be great for you on the beach. You could wear this to dinner next week. Etc." He couldn't have been less interested. He surely owned more designer than any of us could dream of, but he'll never have style. The same thing occured in almost every store. Even in Viktor & Rolf, a man was being practically dressed by his trophy wife. A sad sight.
I think it's worth restating a distinction that someone else made. Logo and designer are (in most cases) clearly separate entities. As that Burberry picture demonstrates, trademark is the furthest thing from fashion. On the other hand, you can tell a cheap, poorly cut suit from the other side of the room. That isn't to say that you need a bespoke suit to look good, but respected designers have earned their reputations for a reason. Someone who is inherently fashionable will probably be able to take a lesser suit to a tailor and have it altered to fit him correctly, but starting with something of quality certainly makes things simpler.
In conclusion, I think the whole issue comes down to thought and preparation. Someone who blindly buys every item they can find with a huge medusa's head or 175 instances of someone's initials can't hope to compete with someone who spent months, if not years, developing their wardrobe from what they pieced together from a variety of sources.